Nitric Acid → N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide

HRID 855793

Reaction equation

HRID 855793 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 95082N-(4-Methoxy-2-methylphenyl)-acetamide

Product 1

HCID 21260362N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamideYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

34 g(0.19 mol) of N-(4-methoxy-2-methylphenyl)acetamide were added in small portions to a mixture of 40 ml of glacial acetic acid and 70 ml of fuming nitric acid at −10 to −15° C. These portions were such that the temperature did not rise above −10° C. The reaction mixture was then poured onto ice. The resulting precipitate was filtered off with suction and washed with water, ethanol and diethyl ether. 22.5 g (53%) of the desired product were obtained.

Workup

  1. customdid not rise above −10° C
  2. additionThe reaction mixture was then poured onto ice
  3. filtrationThe resulting precipitate was filtered off with suction
  4. washwashed with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-a9382db83abc43b581f2ceecf610637b
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Linked notes

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